Trifluoroacetic acid → 3-(azetidin-3-yloxy)pyridine

HRID 2180244Notes

Reaction equation

HRID 2180244 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:9][CH:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24902674HCID 24902674, compound

Product 1

HCID 102195283-(azetidin-3-yloxy)pyridineYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 160 mg (0.64 mmol) of 3-(1-t-butoxycarbonyl-3-azetidinyloxy)-pyridine was added 6 mL of solution containing 3 mL of TFA and 3 mL of CH2Cl2 at ice-bath temperature. The reaction solution was slowly warmed to room temperature and allowed to stir 50 min at room temperature. After 50 min, solvents were removed in vacuo and the crude product was purified by flash chromatography (9:1: 0.05, CHCl3: MeOH:conc. NH4OH) to obtain 62 mg (67%) of a white solid: 1H NMR (300 MHz, CD3OD) δ 8.23 (2H, br s), 7.38 (2H, br d), 5.24 (2H, br s), 4.58 (2H, br d), 4.20 (2H, br d, J=9.8 Hz); Mass spectrum (ESI) m/z 151.7 (M+H+).

Workup

  1. waitAfter 50 min
  2. customsolvents were removed in vacuo
  3. customthe crude product was purified by flash chromatography (9:1: 0.05, CHCl3: MeOH:conc. NH4OH)

Sources & evidence

ORD record
ord-b632f9a39d7848d792d00150d77d8583
Source dataset
uspto-grants-2005_05
Patent number
US06888001B2

Reaction notes

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